If I had to describe the year 2020 in one sentence, I would say that it was a year where absolutely nothing went according to plan — and everything unexpected happened.
“There are decades where nothing happens; and there are weeks where decades happen.”
I’ve been doing an annual review process every year since 2013 for personal reflection and learning. This allows me to ensure I’ve taken on the learnings of the year as well as understand what to start, stop or continue into a new year as I set new goals. I’ve been publicly sharing these since 2014 and mostly do it for me. If you find this valuable or have any questions, I’d love to hear from you on Twitter once you’ve read it.
Suffice to say, this tweet said it best:
For me, like many of us, 2020 was a marathon of stress and uncertainty. Never sure what was lying around the next corner. A deadly pandemic, national civil unrest or murder hornets (yes really).
While I shouldered this same uncertainty and ‘WTF-is-happening-ness’ as many others, the main source of my stress was getting out of my business partnership while simultaneously trying to keep the business running.
I’d describe this process as trying to ride a bike while juggling while rubbing my stomach all at the same time — whilst in the midst of a global pandemic.
What is life teaching me?
When dealing with challenges and hard times it’s easy to let yourself slip into a negative headspace. I spent much of the year in this headspace as I saw my business and everything I had worked to build falling apart. It was like a black cloud above me that followed me around and was a heavy weight on my mind.
I delayed and paused much of the other parts of my life as it was all-consuming. If I wasn’t consumed by that, I’d watch the news and doomscroll on social media.
Throughout the year there were moments where the black cloud would dissipate. I was able to look at these “bad” things that happened and think “what is life trying to teach me here?”
When I got out of the “woe is me” headspace and asked myself what lesson I should be learning here? It flipped the script on what was going on and helped me think more effectively.
I’m a proponent of things happening for us and not to us. With that in mind, in what way could this be a gift?
When we think of the concept of ‘gifts’ we expect them a certain way. They should come gift wrapped, labelled with our name and given on special occasions.
But that’s not how life works.
Something that looks and feels bad in the moment, oftentimes it’s because we’re too close to it. We need to zoom out to a wider time span to see why this happened the way it did. When this happens we will be able to recognize these events as gifts.
How many times has something happened that was considered bad or negative, only for you to see it as a blessing later? Maybe you were upset about a relationship that didn’t work out. Only to be grateful years later that it didn’t, otherwise we wouldn’t have met the person we are with now.
But it’s only when we zoomed out in time did this become clear.
My guess is that this is where the term a ‘blessing in disguise’ comes from.
So what about these negative events could I see as a blessing? That’s the lens I started to consider with 2020.
As I type this I know some people will be angry, maybe even stop reading because somehow I said a bad event that happened this year could be a gift. No, I’m not saying everything will be good, but we can’t control what happens to us, only how we react to it.
So what about these negative events could I see as a blessing? That’s the lens I started to consider with 2020.
COVID-19 devastating the world and caused record job unemployment. The divide between rich and poor more clear than ever as working from home became a status symbol. One which many service and low-wage workers did not experience. 2020 stoked the flames of racial and political injustice as we became more divided than ever.
We now face an even bigger issues of trying to figure out a new normal amid a still socially distanced world. We’ll be dealing with the aftermath of this for a long time to come, but this article by Morgan Housel gave me hope about what this lead to.
I note that this was bad, but really it was both good and bad — the outcome of getting to own my business fully myself was great, but the process of splitting was not for the faint of heart. I got business divorced and it was extremely stressful, expensive and time consuming. I laid out my business partner buyout and issues in this in-depth 5,000 word essay:
This piece of writing didn’t come from sitting down one day to finally write about it. It came from months of uncertainty, of sleepless nights where the only way I would be able to sleep is by writing. Those late night / early morning writing sessions concluded in a 30+ page google doc of lessons that I turned into the article above.
Silver lining: My experiences allowed me to write one of my best pieces that has been read by over 50,000 people. I’ve gotten a TON of great feedback from those also considering business partnership. If my lessons help 1-2 people make more informed decisions it’ll have been (almost) worth it.
Theft & Embezzlement
At the beginning of 2020 I discovered a member of my team, the inventory & wholesale manager had been embezzling from the company from right under our noses.
Finding out someone you trusted who had been with your company for almost 2 years (!!) could do this is incredibly disappointing. It shakes you to your core because this was not some faceless corporation for whom it would be a decimal point on their balance sheet. This is a small business and tight-knit team where every dollar matters.
While we were a remote team, this team member was one of the few I saw on a more regular basis as we both lived in New York.
He’s not only stolen money and product, he’s made it much more difficult to know who to trust moving forward.
Lesson: This experience taught me two important lessons, trust but verify. Between business partners and employees, I should be doing my due diligence with who I let into my life and business. While I believe in assuming positive intent, I should also remember that not everyone has the same intentions as me.
Additionally, the more important business lesson was that with the right checks and balances in place, this should not have happened. We clearly had big issues with accurately measuring and auditing our inventory, otherwise this smoke and mirrors act wouldn’t be possible. This showed us how much we were missing as far as inventory audits, record-keeping and overall structure.
Silver lining: Given the theft and our profitability being much less, the buyout was less expensive for me than it otherwise could have been. It was also just one more headache that added to my business partner’s reasons to not want to be involved anymore.
Supply Chain issues
Due to COVID-19 our supply chain came to a screeching halt for a few months. We had no inventory of our bestselling products which meant sales dropped significantly.
When production finally started up again, we had issues with huge shipping delays. What used to take 3 weeks was taking 8-10 weeks. On top of that, cash was tight due to dealing with low sales (no inventory), partnership legal fees and the employee theft.
The supply chain issues continued throughout 2020 as different parts of the system faced stress. All the way up to ‘shipaggedon’ over the holidays which left many online stores struggling to get gifts in time for Christmas.
Silver lining? Lagging sales, supply chain issues, well that doesn’t help the value of a company that you’re trying to buy out your partner in. It didn’t look nearly as valuable on paper but I knew I could bet on myself to set us on the right path.
Weddings & Travel
COVID: 2 Lavery Weddings: 0
Well the whole wedding, travel and events industry was pretty screwed this year due to COVID, so I’m grateful that all I missed out on were a wedding and trips — many people had it much worse, however it was still personally disappointing to miss out on seeing family. My little brother was due to get married in Portugal in May which of course didn’t happen either. I’m hopeful that this year will be a better year for seeing family and friends… fingers crossed!
My relationship with Emily
Despite postponing our wedding, cancelled trips and missing out on quality time with family we still had a great year together. That was a gift in itself, one that many of us don’t often get this early in a relationship (some not until retirement!).
It’s easy for your relationship to go well when life is going well. It’s during times of stress that you see what you’re made of. That was 2020 for us. It made me more confident in our relationship because of how we handled issues together. In her words, “we make a good pair because we don’t get stressed about the same things”.
Emily was a rock — tolerating me being distracted, stressed and working a lot during odd hours. Often I would wake up between 3-5am and get up to start work (always making more noise than I thought). Sorry boo
Another bonus of Emily as my partner is having her dad (a retired lawyer), on my side when going through the rollercoaster. While changing business ownership is typically stressful enough, it was even moreso in this case as it was happening alongside my business partner’s divorce. F**king nightmare!
While he wasn’t representing me in an official sense, he was able to offer support throughout — and he hasn’t sent me a bill, yet. Thanks for that David.
[ Speaking of lawyers, if you ever need a divorce attorney in NJ — I have a good one. This firm was just 1 of the 5 different law firms I had to hire in 2020 to deal with all the different BS .]
We made the most of it spending quality time together and doing house projects we had on our to-do list. We built out our deck so we can use our backyard and the dogs love it:
I’m used to traveling for work, but over the last two years since moving to Austin I’ve felt less need or desire to travel if I don’t have to. While COVID made it difficult if not impossible to travel, the only travel I really missed was to see my family in Ireland.
I haven’t missed business travel at all. I would much rather double-down on my connections here than go to another conference and meet new people.
We’re lucky to be living in a vibrant, young and healthy community in Austin. In March when things were tense – we were wiping down our groceries, wearing masks and gloves everywhere and using hand sanitizer like it was going out of style.
By June when we realized we weren’t going anywhere anytime soon we loosened our rules, because we were only seeing a small circle of young, low-risk and health conscious friends who were also being careful. I’m happy we did this because we deepened our friendships here and created rituals that kept us feeling connected and sane during quarantine. It’s funny how simple things like meeting at the coffee shop (Levercraft coffee) or standing weekly dinners become a staple in your week.
I went from stopping going to the gym at the beginning of March to being desperate to get back to it by May. Luckily the gym here, Central Athlete, is a pretty unique gym with personalized coaches. Once they reopened they never had more than 3-5 people working out there at one time due to their reservation system.
Another great thing about Austin is the caliber of people either living here already or moving here. If I could buy stock in a city it would definitely be Austin!
Despite the issue with the one team member who embezzled (hi Alejandro ) the rest of the BestSelf team really held it together during a crazy year. While I was dealing with the buyout and all the other distractions, they kept things running as smoothly as possible. My right-hand man James stepped up and took hold of the reins which was a huge help.
During the months (and months… ) negotiations stalled or moved slowly I journaled a lot to stay sane. One big question was what would change when I was 100% owner?
There were 3 parts to this, what would change for me, the team and the customers?
The immediate benefit to me was total control This gave me the ability to define and direct the vision of the company. However, given my business partner had been mostly MIA for the past 2 years this wouldn’t be a big change than the current situation, besides paperwork.
One thing became clear through writing. I wanted to ensure that my team would also have some piece of the upside so we all have incentives to win. This meant beginning the process of moving the company to a new entity, creating a stock plan for employees so that with any big event (investment, acquisition, etc) we can make it a win/win.
And this is somewhat selfish because the only way I win is with their help and continued support.
Another big step we made last year was getting help in the areas we were weak one of which was our finances. We hired an outside CFO firm, AVL Growth, at the beginning of 2020 and it was the best thing we did. I probably could have avoided some of the earlier issues and challenges we had if they had been on board sooner.
My best investment of the year was becoming 100% owner of BestSelf. While it did involve me taking on a significant amount of personal debt I only did so because I believed so strongly in the future of BestSelf & my team. Luckily I have people in my life that believe in me and I’m very grateful for them taking a chance on me
Aside from this I’ve been diversifying into real-estate, stocks and crypto currencies.
In February 2020 I put a deposit down on my first real estate investment property, a 2-bedroom single-family home that is being built as part of a community across the street. Completion by Q3 of next year.
Thanks to my friend and realtor David Shapiro we got in early. We literally bought the 2nd house on the 2nd appointment they had. Since then all 27 houses have sold, with price increases for every 2 houses sold.
I was a little nervous in March with COVID hitting how it would affect the real estate market although Austin market was barely affected in 2008 with the mortgage crisis so it wasn’t a big enough concern to reconsider. Fortunately the Austin housing market has continued to explode due to people from California and New York moving here.
I had been part of the crypto bull run at the end of 2017 but was only in due to speculation rather than understanding anything about the underlying technology.
In June last year I became part of a private Slack group that my friend Ben started. What began as a welcome distraction from my business woes ended up becoming much more profitable & fun than I’d ever expected. Specifically in the decentralized finance (DeFi) area of crypto on the Ethereum network. Since getting involved in this community I’ve learned so much about staking, yield farming, smart contracts and a bunch of other things that I was previously oblivious to.
It has also changed my opinion on crypto as a store of value and specific use-cases. With the dollar becoming less and less valuable due to the government printing more and more of it I believe crypto will be the currency of the future.
I’ve never been one to put much $$ in individual stocks. That changed in 2020, specifically investing in companies and products I believe in, and would stand up well during COVID.
My biggest winners were Upwork (UPWK), Zoom(ZM), Shopify (SHOP), Bill.com (BILL) & Peloton (PTON).
I know you shouldn’t fall in love with a stock, but baby I just love Peloton. For a stationary bike this thing still gets places! I bought Peloton at IPO in 2019 (having been a customer since 2016) as I believed in the product and what they were building so much. If you review their IPO filing docs their retention rate is 95%. That means for each bike sold you have a bunch of new people now on a $39 monthly subscription.
While the stock dropped after IPO I doubled down whenever COVID hit. I’m bullish on PTON for the long term so I’m holding. However, I learned about options trading in May (much like everyone else with the Robinhood app) and made around 14k from just trading PTON options over the past 6 months.
I used a little of my winnings to upgrade to the new Bike+, details here.
You’ll probably notice a theme with all my purchases, basically making quarantine and staying in the house as comfortable as possible.
1. My Sunlighten 2-Person Infrared sauna. I’ve been using it 3-5 times per week since I got it in September and I’ve made it a habit to read while I’m in there so it’s led me to read a lot more books! I think I read more in 3 months than I did in the previous 9!
Emily calls this the “Tesla of grills” as you can control it on your phone and it’s super easy to use. With us cooking much more at home I’ve been using this a few times a week and it’s amazing.
Been reading much more on Kindle, while I do prefer physical books, the kindle makes note taking easier. The waterproof part makes great for reading in the sauna as regular books can get damaged.
4. Sonos Move
This portable indoor/outdoor speaker is legit amazing. Great sound, you can bring wherever you want and it also natively lets you play podcasts from any app through airplay which my other sonos are way more tricky with. High recommend!
5. Oculus Quest
I got this in March when lockdown started and it was very fun. Although definitely a little dystopian playing VR (with friends) while we were all quarantined in our houses. Since I got it the new Quest 2 came out which is better but it’s a fun experience. Pretty incredible how far the technology has come along over the last few years.
6. Air Fryer
New to us but makes cooking vegetables an absolute breeze. Highly recommend!
Media & Books:
Fiction: The Mandibles
- The Fourth Turning
- The Secret Race
- Billion Dollar Loser (see my review here)
- The Almanack of Naval Ravikant
- Black Swan
- Soul (Disney+)
- Death to 2020 (Netflix)
- The Trial of the Chicago 7 (Netflix)
- The Invisible Man (Amazon)
- We Have No Idea What Happens Next by Morgan Housel
- How 2020 Killed Hard Work by Mike Brown
- 50 Ideas that changed my life by David Perrel
- The case for 500k Bitcoin by Tyler Winklevoss
- How to think for yourself by Paul Graham
- Oatly: The New Coke by Nat Eliason
Where could I have been better?
A huge one was my inability to let go of things that were way beyond my control. There were times throughout the year where I let the concern over things with business and the partnership buyout cloud over my day to day life. It resulted in me pausing lots of areas of my life until it was over.
“NARRATOR (in Morgan Freeman voice): She thought it would be over any day. She was very wrong.”
Had I known in March that this thing would still be going on in September I may have acted differently. However it was one of those situations that was constantly in “almost done” status. Oh it’ll be next Monday we sign, then next week comes and it’s pushed until Wednesday, then Friday, and then it’s pushed again to the next week. On and on and on, for months.
I let my worry and ever-consuming partner issues cloud my judgement and habits. I became reactive instead of proactive as I let my routines slide and bad habits spiral. Much like many of us did in quarantine, I drank alcohol more often than was normal for me. The ability to craft a delicious old fashioned from the comfort of your own home is both a blessing and a curse .
Between increased stress and drinking, my sleep was negatively affected. Months of surviving on 4-5 hours per night. The lack of sleep made me skip working out more often. We would order in or eat fast food more often due to not planning meals ahead of time. By the time we got hangry we would eat the easiest and quickest option. It was a vicious cycle.
This was one of the big aspects I planned to work on going into 2021.
Start, Stop & Continue in 2021
Before I set any goals I want to decide what I’ll Start, Stop & Continue.
Work outside of my house – I got an office!
After 6 years of working from my house (and coffee shops) I’ve decided to get an office!
I realized during quarantine that because I wasn’t leaving the house much I lacked boundaries, so I worked a lot. I also made a recent hire that I’ll be working with in-person and I’d rather have a dedicated space for work, filming etc.
It’s a private office inside a local coworking space. The great thing is that it’s 1.5 miles from my house, and right next to my gym. This removes a lot friction for focusing on health.
This is the before picture (will share after soon – putting finishing touches to it):
Consistent with my workouts
I was on and off the workout wagon towards the end of the year. This was as a result of stress, not sleeping as well and being so busy with work.
This year I want to make moving my body everyday a non-negotiable, both at the gym and getting outside. The 3-mile round trip walk to and from my office will be a nice change of pace.
Writing & Creating — on a set schedule
Journaling and writing have helped me with getting clearer on both thinking and decision making. I took part in David Perell’s Write of Passage which was a great jumping off point that I plan to do more of in 2021.
This means creating a daily writing habit and publishing on a schedule.
Earlier bedtime & consistent sleep schedule
It’s not only kids who benefit from a bedtime routine or going to bed at the same time. I’ve been doing this for the last couple of weeks and can see how much of a difference it makes for both my energy and mood.
Now I just need to sell Emily on the idea of being in bed by 10pm
I want to dedicate more time to thinking and ideation. This likely means outside or in nature, with nothing to distract me (phone, book, podcasts etc) – just a pen and a notebook.
Less screentime & social media in general
I realized how much time I was wasting “doomscrolling” through social media on a endless loop. I want to do less of that this year and be more intentional with my time.
Drinking so often
We got into a habit of having an old-fashioned in the evening or wine with dinner a little too often in 2020. It wasn’t that we would drink a lot. Yet, even 1 drink was a catalyst for other negative effects like staying up late and worse quality sleep. Which led to not having as much energy the next day.
Lifehack: If you don’t want to drink as many old fashioned, don’t have the big ice cubes in the freezer. We started leaving the mould out of the freezer. This way, if we thought we may slip, it would take at least 4 hours to be able to make one — by then the feeling would have passed.
Having as many work meetings
I find work meetings draining, even when I enjoy who I work with — zoom fatigue is real. I have a couple of calls per week that I do via phone and I enjoy those much more as I can do them while walking outside. In 2021 I’ll be both decreasing my number of calls and also doing more meetings by phone, old school style.
Reading & Sauna
For the last few months I’ve been starting my day with 30 mins in the infrared sauna and reading a book (new waterproof Kindle). Or occasionally watching a class on something I want to learn. I want to continue this in 2021 as it was a great way to start the day.
Intentional social time with friends
I want to have more small dinners with friends, both one’s I want to get to know better and deepening those I already have. Over the new years Emily and I made a list of people we want to socialize with more this year.
During quarantine we started cooking more at home together and I also got a Traeger grill (it’s amazing). I want to continue to cook more moving forward, but also to learn new recipes so it’s not the same stuff all the time.
2021 Goal Setting
I typically add my goals at the end of my reflection, however given how long this was already I wanted to share my reflections and new a new article just on goals an habits in the new year. This will be coming next week!
Hope you enjoyed this reflection, if you have any comments just tweet at me 🙂